IE41918L - 3-thio-cephalosporins. - Google Patents
3-thio-cephalosporins.Info
- Publication number
- IE41918L IE41918L IE752297A IE229775A IE41918L IE 41918 L IE41918 L IE 41918L IE 752297 A IE752297 A IE 752297A IE 229775 A IE229775 A IE 229775A IE 41918 L IE41918 L IE 41918L
- Authority
- IE
- Ireland
- Prior art keywords
- cephem
- nitrobenzyl
- phenyl
- substituted
- tetrazol
- Prior art date
Links
- 229940124587 cephalosporin Drugs 0.000 title 1
- -1 1-methyl-1H-tetrazol-5-yl Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 229940088710 antibiotic agent Drugs 0.000 abstract 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 abstract 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 2
- MJSLXMHHSSCUOK-LRTDYKAYSA-N (4-nitrophenyl)methyl (6r)-3-chloro-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)C1=C(Cl)CS[C@H]2N1C(=O)C2NC(=O)CC1=CC=CS1 MJSLXMHHSSCUOK-LRTDYKAYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- RIZIMSRFCCGYOH-CYBMUJFWSA-N [(6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CN2C(=O)C[C@H]2SC1 RIZIMSRFCCGYOH-CYBMUJFWSA-N 0.000 abstract 1
- IYZOZZXIIZIBFS-SSDOTTSWSA-N [(6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl] methanesulfonate Chemical compound S1CC(OS(=O)(=O)C)=CN2C(=O)C[C@H]21 IYZOZZXIIZIBFS-SSDOTTSWSA-N 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001356 alkyl thiols Chemical class 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 150000001782 cephems Chemical group 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
7-Acylamido-3-cephem-4-carboxylic acid antibiotics directly substituted in the 3-position of the cephem ring system with a sulfur atom bonded to a 5- or 6-membered heterocyclic ring, a lower alkyl group, or a phenyl or substituted phenyl group are prepared with the corresponding 3-halo-3-cephem esters. For example, p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate reacts with 1-methyl-1H-tetrazol-5-ylthiol to provide p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-[(1-methyl-1H-tetrazol-5-yl)thio]-3-cephe m-4-carboxylate. The p-nitrobenzyl ester group is removed by catalytic hydrogenolysis to provide the antibiotic carboxylic acid compound. Alternatively, the antibiotics are prepared by reacting a 3-alkylsulfonyloxy, or 3-arylsulfonyloxy-3-cephem, for example, 3-methanesulfonyloxy-3-cephem, or a 3-p-toluenesulfonyloxy-3-cephem with the heterocyclic thiol, the phenyl or substituted phenylthiol, or with the lower alkylthiol.
[US3992377A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/532,431 US3992377A (en) | 1974-12-13 | 1974-12-13 | 3-Thio-substituted cephalosporin antibiotics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41918L true IE41918L (en) | 1976-06-13 |
| IE41918B1 IE41918B1 (en) | 1980-04-23 |
Family
ID=24121771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2297/75A IE41918B1 (en) | 1974-12-13 | 1975-10-22 | 3-thio-substituted cephalosporin antibiotics |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3992377A (en) |
| JP (1) | JPS5182292A (en) |
| BE (1) | BE836565A (en) |
| CA (1) | CA1039270A (en) |
| CH (1) | CH620216A5 (en) |
| DE (1) | DE2555858A1 (en) |
| FR (1) | FR2293935A1 (en) |
| GB (1) | GB1526978A (en) |
| IE (1) | IE41918B1 (en) |
| IL (1) | IL48341A (en) |
| NL (1) | NL7514557A (en) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH605997A5 (en) * | 1974-08-30 | 1978-10-13 | Ciba Geigy Ag | |
| ZA766941B (en) * | 1975-11-21 | 1978-06-28 | Merck & Co Inc | 3-(substituted thio)cephalosporins,derivatives and nuclear analogues thereof |
| US4150156A (en) * | 1975-11-21 | 1979-04-17 | Merck & Co., Inc. | 7-(Substituted methyl)-3-(substituted thio)-cephalosporins, derivatives and pharmaceutical compositions containing them |
| US4197402A (en) * | 1976-08-09 | 1980-04-08 | Shionogi & Co., Ltd. | Cephalosporin analogues |
| JPS53103493A (en) * | 1977-02-18 | 1978-09-08 | Takeda Chem Ind Ltd | Cephalosporin derivatives and process for their preparation |
| FR2418233A2 (en) * | 1978-02-22 | 1979-09-21 | Roussel Uclaf | Antibiotic syn isomers of oxime(s) - of 3-alkylthio or acylamino 7-amino thiazolyl acetamido cephalosporanic acids |
| US4739048A (en) * | 1980-05-29 | 1988-04-19 | Merck & Co., Inc. | Process for the preparation of thienamycin and intermediates |
| US4745188A (en) * | 1980-11-21 | 1988-05-17 | Merck & Co., Inc. | Process for preparing 3-substituted-6-substituted-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| GR76342B (en) * | 1981-02-02 | 1984-08-06 | Fujisawa Pharmaceutical Co | |
| JPS5984890A (en) | 1982-11-05 | 1984-05-16 | Hisayasu Ishimaru | Cephalosporin compound for oral administration |
| FR2550200B1 (en) * | 1983-08-01 | 1988-04-08 | Fujisawa Pharmaceutical Co | PROCESS FOR THE PREPARATION OF CEPHEM COMPOUNDS WITH ANTIMICROBIAL ACTIVITY AND NOVEL PRODUCTS THUS OBTAINED |
| JPH0686459B2 (en) * | 1989-12-07 | 1994-11-02 | 明治製菓株式会社 | Process for producing 3-substituted thio-3-cephem compound |
| JP2857532B2 (en) * | 1992-03-12 | 1999-02-17 | 明治製菓株式会社 | New cephalosporin derivatives |
| US5698547A (en) * | 1994-04-01 | 1997-12-16 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| LT4193B (en) | 1994-04-01 | 1997-07-25 | Microcide Pharmaceuticals Inc | Cephalosporin antibiotics |
| US5688786A (en) * | 1994-04-01 | 1997-11-18 | Microcide Pharmaceuticals, Inc. | β-lactam antibiotics |
| JPH09511738A (en) * | 1994-04-01 | 1997-11-25 | マイクロサイド・ファーマシューティカルズ・インコーポレーテッド | Cephalosporin antibiotics |
| US5551306A (en) * | 1994-12-06 | 1996-09-03 | Hersey Measurement Company | Magnetic flowmeter |
| WO1996017850A1 (en) * | 1994-12-09 | 1996-06-13 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds and pharmaceutical use thereof |
| AU5985596A (en) * | 1995-05-31 | 1996-12-18 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| MY127641A (en) * | 1995-10-12 | 2006-12-29 | Essential Therapeutics Inc | Cephalosporin antibiotics |
| AUPN801196A0 (en) * | 1996-02-12 | 1996-03-07 | Fujisawa Pharmaceutical Co., Ltd. | New cephem compounds and pharmaceutical use thereof |
| US6025352A (en) * | 1997-09-29 | 2000-02-15 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| US6030965A (en) * | 1997-09-30 | 2000-02-29 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| AR035728A1 (en) * | 2001-01-16 | 2004-07-07 | Merck & Co Inc | PERFECTED PROCESS FOR CARBAPENEM SYNTHESIS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
-
1974
- 1974-12-13 US US05/532,431 patent/US3992377A/en not_active Expired - Lifetime
-
1975
- 1975-10-17 CA CA237,876A patent/CA1039270A/en not_active Expired
- 1975-10-22 IE IE2297/75A patent/IE41918B1/en unknown
- 1975-10-22 IL IL48341A patent/IL48341A/en unknown
- 1975-12-09 JP JP50146818A patent/JPS5182292A/en active Pending
- 1975-12-09 GB GB50321/75A patent/GB1526978A/en not_active Expired
- 1975-12-11 DE DE19752555858 patent/DE2555858A1/en not_active Withdrawn
- 1975-12-11 BE BE1007077A patent/BE836565A/en unknown
- 1975-12-12 CH CH1616275A patent/CH620216A5/de not_active IP Right Cessation
- 1975-12-12 FR FR7538212A patent/FR2293935A1/en active Granted
- 1975-12-12 NL NL7514557A patent/NL7514557A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IE41918B1 (en) | 1980-04-23 |
| JPS5182292A (en) | 1976-07-19 |
| IL48341A (en) | 1980-05-30 |
| FR2293935B1 (en) | 1979-09-21 |
| FR2293935A1 (en) | 1976-07-09 |
| DE2555858A1 (en) | 1976-06-16 |
| NL7514557A (en) | 1976-06-15 |
| IL48341A0 (en) | 1975-12-31 |
| CH620216A5 (en) | 1980-11-14 |
| CA1039270A (en) | 1978-09-26 |
| US3992377A (en) | 1976-11-16 |
| GB1526978A (en) | 1978-10-04 |
| BE836565A (en) | 1976-06-11 |
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